A Canadian artist who’s deeply rooted in the French chanson tradition, Pierre Lapointe splits his time between Montreal and Paris—making him well acquainted with winter. “I’m lucky to experience two different winters,” he says. “A rainy one and a snowier one.” What the two have in common, he explains, is a special kind of melancholy inspired by the short days, long nights, and chill in the air. It’s something reflected in his picks here, which center on vulnerability and reflection.